I have been reading Letters of J.R.R. Tolkien and I can't help but get the impression that he was not particularly fond of Americans. Just as one example, here is a quote from Letter #328, which is in regards to American hippies loving his books:
The horrors of the American scene I will pass over, though they have given me great distress and labour. (They arise in an entirely different mental climate and soil, polluted and impoverished to a degree only paralleled by the lunatic destruction of the physical lands which Americans inhabit.)....
Edit: He also seems to make fun of American kids who say 'Gee Whiz', says Americans can't handle criticism, and has a particular loathing for Disney, which he seems to equate with American popular culture.
This Blog post says a lot with sources to his letters. It concludes with, "It is important to remember that Tolkien had never been to America in his life. His comments are thus particularly valuable as a source for studying stereotyped images of America among Englishmen of a certain age and cast of thought, although they are of course that much less valuable as a source for actual knowledge about America."
It does appear that Tolkin may have not liked America, but it was not due to personal experience with it. I don't know of any specific instances of his relationship with actual Americans, except Joy Davidman. Joy put great strain on J.R.R Tolkien and C.S. Lewis's relationship, although the depth of their friendship outlasted that strain. However, there are many other reasons for Joy to put the strain on before her being an American, things like her divorce.
I would probably liken J.R.R. Tolkien's view of America to be like an American's stereotypical view of China.
I think it's important to keep in mind that J.R.R Tolkien absolutely loved rural England. A lot of the events of Lord of the Rings can be considered metaphors for the destruction of peaceful rural England being consumed by industrialization. SPOILERS!! At the end of The Return of the King, Frodo and the Hobbits return to the shire only to find it's been taken over by evil forces who are forcing it's inhabitants to industrialize the Shire.
In fact, of the destruction of rural England he once said:
Tolkien lived most of his life in Oxfordshire, the almost perfect stereotype of old school England, hedgerows, thatched cottages, millponds and waterwheels etc, and he famously rode a bicycle around because he hated cars so much.
One reason he disliked America is because he associated it with rising 'Hippie' counter-culture. When his books became popular in the 50's and 60's a lot of people mistook the central messages and themes as tacit approval for a socialist revolution. They thought the Shire represented a rejection of capitalism and how people could live more harmoniously without it. The high fantasy aspect of dragons and wizards and the like also appealed to that 'Hippie' culture. Famously, Led Zeppelin were fans of his works and there were rumours that Stairway to Heaven was a song about Galadriel. It isn't, but their song Ramble On was inspired by Lord of the Rings.
I'm not going to defend his views, it's pretty stupid to judge an entire nation of peoples based on a small minority, but consider his situation in the 1960's. He was fairly old by then, in his seventies, and suddenly his fiction works were receiving huge attention. Initially he quite liked the attention and would answer all the fain mail he could, but he quickly grew tired of explaining over and over that the books were not pro-Communist or anti-Capitalist. He eventually had his phone number removed from the directory because he was so tired of the attention. He was also a renowned Old English and medieval scholar who wrote exhaustively about Norse and Germanic mythology which was no where near as popular as his fiction works. It was his expertise in Norse literature which lead to him being accused of having racist and potentially pro-Nazi and pro-Aryan feelings during WWII. He was actually a staunch anti-racist, even speaking out against South African apartheid, but mud like that sticks no matter what.
Again, I'm not going to defend what he wrote, but it's easy to see how he could become a crotchety old man, disillusioned by his new young fan base, who mistakenly saw his works as a political statement.
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I would make the suggestion of asking a more targeted audience at /r/tolkienfans.
It's relevant in this context that Mordor - the leading industrial and military power - has great mines and military power in the north, and slave-worked agricultural fields in the south.
But Tolkien in general doesn't like modernism and he doesn't like industrialization. He is a 19th century romantic who likes forests, trees, and a sort of communitarianism. To the extent he doesn't like the US, it is because it embodies modernism and industrialization; change and disruption. He also doesn't like industrial Britain, as far as that goes.
You can see the anti-industrialization in the "scouring of the shire". Or in Treebeard's description of Saruman as someone with a mind of "metal and gears" who doesn't care for growing things. And in how Saruman cuts down Fangorn Forest to "feed the fires of Orthanc".
For Tolkien, the ideal world consisted of small, pre-modern agrarian villages, largely self-sufficient. Its antithesis would be a large, uniform, continent-spanning industrialized power.
Tolkien's ideas probably had their genesis in his WWI experience of total, mechanized war (in a forward to LOTR, he mentions that all but one of his close friends was dead by 1918); they aren't specifically directed at the US. But again, if your ideal is the premodern English hamlet...well, you're not going to find much of that in 20th century America.
For an extensive treatment of this theme, look at Patrick Curry's Defending Middle-earth: Tolkien, Myth and Modernity (2004).
In addition to the personal reasons mentioned by other comments, America's position as an industrial giant couldn't have helped. Its clear from his stories that he was extremely critical of industrialization(see: Isengard and Mordor, areas where the environment is exploited in the name of production).
While he recognized and admonished Europe's industrial metamorphosis, America is a special case as country born of Industry, having become a major economic power due in part to their military industry supplying war in Europe. Their industrial products scoured the European landscape and population, perhaps epitomizing the corrupting force of industrialization as much as Hitler's Germany.
While this wouldn't lead him to categorically dislike America, the country's history certainly would have made some impact (consciously or not) on Tolkien's opinion given his rather outspoken views.
It's been a while since I did the serious Tolkien research in my life, so there's that warning out of the way.
There have been some links to Tolkien's particular characterization of hobbits and his friendship with an American from Appalachia.
Have two links:
http://historynewsnetwork.org/blog/13541
http://www.wsfa.org/journal/j79/2/index.htm
A short version is that it may be the reason they grow their own pipe weed and talk the way they do, though it's been difficult to prove this -- the fact that Tolkien was friends with an Appalachian man is, at least, more easily confirmed.
This would make sense, though, given what everyone else has pointed out. In the eastern part of America Appalachia is easily the most rural and isolated, the most like what Tolkien thought he was losing in England. The crippling poverty and such like would have been less obvious to someone from another country, I suppose...